AU693285B2 - Pyridine modulators of acetylcholine receptors - Google Patents
Pyridine modulators of acetylcholine receptorsInfo
- Publication number
- AU693285B2 AU693285B2 AU39544/95A AU3954495A AU693285B2 AU 693285 B2 AU693285 B2 AU 693285B2 AU 39544/95 A AU39544/95 A AU 39544/95A AU 3954495 A AU3954495 A AU 3954495A AU 693285 B2 AU693285 B2 AU 693285B2
- Authority
- AU
- Australia
- Prior art keywords
- hydrogen
- substituted
- methyl
- alkynyl
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 108010009685 Cholinergic Receptors Proteins 0.000 title claims abstract description 34
- 102000034337 acetylcholine receptors Human genes 0.000 title claims abstract description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 61
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 206010012289 Dementia Diseases 0.000 claims abstract description 12
- 208000002193 Pain Diseases 0.000 claims abstract description 10
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 9
- 230000036407 pain Effects 0.000 claims abstract description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 212
- 239000001257 hydrogen Substances 0.000 claims description 207
- 150000002431 hydrogen Chemical group 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- -1 cyano, cyanomethyl Chemical group 0.000 claims description 98
- 125000000304 alkynyl group Chemical group 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 85
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 75
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 54
- 125000003107 substituted aryl group Chemical group 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 28
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 229960002715 nicotine Drugs 0.000 claims description 18
- 125000003435 aroyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- AUBPMADJYNSPOA-UHFFFAOYSA-N Anabaseine Chemical compound C1CCCC(C=2C=NC=CC=2)=N1 AUBPMADJYNSPOA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229930014345 anabasine Natural products 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- UIKROCXWUNQSPJ-VIFPVBQESA-N (-)-cotinine Chemical compound C1CC(=O)N(C)[C@@H]1C1=CC=CN=C1 UIKROCXWUNQSPJ-VIFPVBQESA-N 0.000 claims description 4
- MYKUKUCHPMASKF-VIFPVBQESA-N (S)-nornicotine Chemical compound C1CCN[C@@H]1C1=CC=CN=C1 MYKUKUCHPMASKF-VIFPVBQESA-N 0.000 claims description 4
- WHAIHNKQZOMXJJ-NSHDSACASA-N 3-[(2s)-1-methylpiperidin-2-yl]pyridine Chemical compound CN1CCCC[C@H]1C1=CC=CN=C1 WHAIHNKQZOMXJJ-NSHDSACASA-N 0.000 claims description 4
- SOPPBXUYQGUQHE-JTQLQIEISA-N Anatabine Chemical compound C1C=CCN[C@@H]1C1=CC=CN=C1 SOPPBXUYQGUQHE-JTQLQIEISA-N 0.000 claims description 4
- SOPPBXUYQGUQHE-UHFFFAOYSA-N Anatabine Natural products C1C=CCNC1C1=CC=CN=C1 SOPPBXUYQGUQHE-UHFFFAOYSA-N 0.000 claims description 4
- UIKROCXWUNQSPJ-UHFFFAOYSA-N Cotinine Natural products C1CC(=O)N(C)C1C1=CC=CN=C1 UIKROCXWUNQSPJ-UHFFFAOYSA-N 0.000 claims description 4
- WHAIHNKQZOMXJJ-UHFFFAOYSA-N N-Methylanabasine Natural products CN1CCCCC1C1=CC=CN=C1 WHAIHNKQZOMXJJ-UHFFFAOYSA-N 0.000 claims description 4
- MYKUKUCHPMASKF-UHFFFAOYSA-N Nornicotine Natural products C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229950006073 cotinine Drugs 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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- 239000002243 precursor Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- DPNGWXJMIILTBS-UHFFFAOYSA-N myosmine Chemical compound C1CCN=C1C1=CC=CN=C1 DPNGWXJMIILTBS-UHFFFAOYSA-N 0.000 claims 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
- 208000035475 disorder Diseases 0.000 abstract description 16
- 150000003222 pyridines Chemical class 0.000 abstract description 15
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- IWIPOXSHIIAUKI-UHFFFAOYSA-N tert-butyl 2-(5-bromopyridin-3-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C1=CN=CC(Br)=C1 IWIPOXSHIIAUKI-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- PQBLBAOOMKDESK-UHFFFAOYSA-N trimethyl-[5-(1-methylpyrrolidin-2-yl)pyridin-3-yl]silane Chemical compound CN1CCCC1C1=CN=CC([Si](C)(C)C)=C1 PQBLBAOOMKDESK-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US485398 | 1990-02-26 | ||
| US337640 | 1994-11-10 | ||
| US08/337,640 US5594011A (en) | 1994-11-10 | 1994-11-10 | Modulators of acetylcholine receptors |
| US08/485,398 US5703100A (en) | 1994-11-10 | 1995-06-07 | Modulators of acetylcholine receptors |
| PCT/US1995/013068 WO1996015123A1 (fr) | 1994-11-10 | 1995-10-16 | Modulateurs a base de pyridine agissant sur les recepteurs de l'acetylcholine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3954495A AU3954495A (en) | 1996-06-06 |
| AU693285B2 true AU693285B2 (en) | 1998-06-25 |
Family
ID=26990807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU39544/95A Ceased AU693285B2 (en) | 1994-11-10 | 1995-10-16 | Pyridine modulators of acetylcholine receptors |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5703100A (fr) |
| EP (1) | EP0739342B1 (fr) |
| JP (1) | JP3802928B2 (fr) |
| AT (1) | ATE248160T1 (fr) |
| AU (1) | AU693285B2 (fr) |
| CA (1) | CA2180843C (fr) |
| DE (1) | DE69531603T2 (fr) |
| ES (1) | ES2204968T3 (fr) |
| WO (1) | WO1996015123A1 (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977144A (en) * | 1992-08-31 | 1999-11-02 | University Of Florida | Methods of use and compositions for benzylidene- and cinnamylidene-anabaseines |
| US7048906B2 (en) | 1995-05-17 | 2006-05-23 | Cedars-Sinai Medical Center | Methods of diagnosing and treating small intestinal bacterial overgrowth (SIBO) and SIBO-related conditions |
| US6562629B1 (en) | 1999-08-11 | 2003-05-13 | Cedars-Sinai Medical Center | Method of diagnosing irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth by detecting the presence of anti-saccharomyces cerivisiae antibodies (asca) in human serum |
| US6861053B1 (en) | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
| US5629325A (en) * | 1996-06-06 | 1997-05-13 | Abbott Laboratories | 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission |
| US6362009B1 (en) | 1997-11-21 | 2002-03-26 | Merck & Co., Inc. | Solid phase synthesis of heterocycles |
| CA2334186A1 (fr) * | 1998-06-05 | 1999-12-09 | Regent Court Technologies | Inhibiteurs de monoamine oxydase (mao) et leurs utilisations |
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| US20030162770A1 (en) | 2002-02-22 | 2003-08-28 | Davis Bonnie M. | Use of modulators of nicotinic receptors for treatment of cognitive dysfunction |
| JP4679514B2 (ja) | 2003-04-24 | 2011-04-27 | メルク・シャープ・エンド・ドーム・コーポレイション | Ａｋｔ活性の阻害剤 |
| CN1809354A (zh) | 2003-04-24 | 2006-07-26 | 麦克公司 | Akt活性抑制剂 |
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| JP4639327B2 (ja) * | 2004-07-16 | 2011-02-23 | 国立大学法人高知大学 | 光学活性アミノピリジル基含有ピロリジン誘導体及びそれを用いた不斉合成方法 |
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| JP2020503950A (ja) | 2017-01-06 | 2020-02-06 | クロノ セラピューティクス インコーポレイテッドＣｈｒｏｎｏ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 経皮薬剤送達の装置及び方法 |
| LT3762368T (lt) | 2018-03-08 | 2022-06-10 | Incyte Corporation | Aminopirazindiolio junginiai, kaip pi3k-γ inhibitoriai |
| CA3101966A1 (fr) | 2018-05-29 | 2019-12-05 | Morningside Venture Investments Limited | Procedes et systemes d'administration de medicament |
| WO2020010003A1 (fr) | 2018-07-02 | 2020-01-09 | Incyte Corporation | DÉRIVÉS D'AMINOPYRAZINE UTILISÉS EN TANT QU'INHIBITEURS DE PI3K-γ |
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| US3247213A (en) * | 1961-04-12 | 1966-04-19 | Shell Oil Co | Heterocyclic nitrogen compounds |
| NL7008619A (fr) * | 1969-06-25 | 1970-12-29 | Merck & Co Inc | |
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| CA2080536A1 (fr) * | 1991-10-17 | 1993-04-18 | John S. Ward | Activite nicotinique d'une serie d'arecolones et d'isoarecolones |
| US5242935A (en) * | 1992-03-06 | 1993-09-07 | R. J. Reynolds Tobacco Company | Method for treatment of neurodegenerative diseases |
| US5187169A (en) * | 1992-04-10 | 1993-02-16 | R. J. Reynolds Tobacco Company | Method for treatment of neurodegenerative diseases |
| US5276043A (en) * | 1992-04-10 | 1994-01-04 | R. J. Reynolds Tobacco Company | Method for treatment of neurodegenerative diseases |
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| DE69332641T2 (de) * | 1992-08-31 | 2003-11-27 | University Of Florida Research Foundation, Inc. | Anabasein derivate zur behandlung von degenerativen erkrankungen des nervensystems |
-
1995
- 1995-06-07 US US08/485,398 patent/US5703100A/en not_active Expired - Lifetime
- 1995-10-16 AU AU39544/95A patent/AU693285B2/en not_active Ceased
- 1995-10-16 EP EP95937421A patent/EP0739342B1/fr not_active Expired - Lifetime
- 1995-10-16 ES ES95937421T patent/ES2204968T3/es not_active Expired - Lifetime
- 1995-10-16 AT AT95937421T patent/ATE248160T1/de not_active IP Right Cessation
- 1995-10-16 CA CA002180843A patent/CA2180843C/fr not_active Expired - Fee Related
- 1995-10-16 WO PCT/US1995/013068 patent/WO1996015123A1/fr active IP Right Grant
- 1995-10-16 JP JP51556696A patent/JP3802928B2/ja not_active Expired - Fee Related
- 1995-10-16 DE DE69531603T patent/DE69531603T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69531603D1 (de) | 2003-10-02 |
| ES2204968T3 (es) | 2004-05-01 |
| AU3954495A (en) | 1996-06-06 |
| US5703100A (en) | 1997-12-30 |
| EP0739342B1 (fr) | 2003-08-27 |
| JP3802928B2 (ja) | 2006-08-02 |
| DE69531603T2 (de) | 2004-06-24 |
| EP0739342A1 (fr) | 1996-10-30 |
| CA2180843A1 (fr) | 1996-05-23 |
| CA2180843C (fr) | 2003-07-15 |
| JPH09508648A (ja) | 1997-09-02 |
| ATE248160T1 (de) | 2003-09-15 |
| WO1996015123A1 (fr) | 1996-05-23 |
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